Methyl iodide → (2-Cyclopropyl-4-methyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidin-6-yl)-acetic acid ethyl ester

HRID 57794Notes

Reaction equation

HRID 57794 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:11](=[O:12])[N:10]2[N:13]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[CH:15]=[C:9]2[NH:8][CH:7]=1)[CH3:2].[H-].[Na+].[CH3:22]I>O1CCCC1.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:11](=[O:12])[N:10]2[N:13]=[C:14]([CH:16]3[CH2:17][CH2:18]3)[CH:15]=[C:9]2[N:8]([CH3:22])[CH:7]=1)[CH3:2]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178470741HCID 178470741, compound

Product 1

HCID 86702935(2-Cyclopropyl-4-methyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidin-6-yl)-acetic acid ethyl esterYield 59%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (2-cyclopropyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidin-6-yl)-acetic acid ethyl ester (80 mg, 0.3 mmol, 1 eq) described in example 90 in tetrahydrofuran (2 mL) was added sodium hydride (16 mg, 3.9 mmol, 1.3 eq). The mixture was stirred during 30 min at room temperature and methyl iodide (30 μL, 0.5 mmol, 1.5 eq) was added. The mixture was stirred at room temperature for 5 h. The mixture was then diluted with ethyl acetate (5 mL) and water (5 mL) was added. The aqueous layer was extracted with ethyl acetate (2×10 mL) and the aqueous phases were dried over magnesium sulfate, filtered and evaporated in vacuo. The crude residue was purified by flash chromatography using cyclohexane and ethyl acetate (100/0 to 0/100) to afford the expected compound as white powder (16 mg, 59% yield).

Workup

  1. stirringThe mixture was stirred at room temperature for 5 h
  2. additionwas added
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  4. dry with materialthe aqueous phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-30351e5ad1044d5ab24c54b5b25da183
Source dataset
uspto-grants-2016_09
Patent number
US09434745B2

Reaction notes

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